Staple #16: The Slim Dark Jeans

Unlike other Staples such as the suit, the V-neck sweater, or the navy jacket, I don’t need to invest any time in trying to convince men why they should be wearing jeans. 99.9% of men already do and are happy to do so. And, while a pair of jeans is as ubiquitous as it gets when it comes to men and clothing, there is a right way to wear them so they’re still stylish.

Joe Biden dad jeans

We’ve all seen dad jeans like those pictured above. They’re as bad as a pair of baggy cargo shorts and there’s nothing else you can wear that can make bad jeans look good. Even if you nail the fit and coloring of everything else you have on that day, dad jeans look ridiculous. There are a few key rules to follow to make sure your jeans look as good as they can.

Opt for a dark, inky blue. One of the strongest habits men have is wearing jeans when they need to appear more dressed up than they actually are. A good workaround for this is getting your jeans in a dark color. This makes them look more formal and will give you more situations in which you can wear them. It’s still not something you’ll want to have on at the opera or a board meeting, but darker jeans are acceptable in many business-casual environments and other events like dinner parties or nights out on the prowl.

construction cone 180

Another benefit to darker jeans is that they’re not inappropriate in a casual environment either. I can have mine on for a session at the skatepark and not look like I’m the overdressed idiot who doesn’t understand a casual situation.

Wear them in a slim fit. This rule applies regardless of your size. The days of Jnco’s and boot-cut jeans being good alternatives are dead and gone – and good riddance. Slim doesn’t mean emo-I-raided-my-sister’s-closet skinny. It means they’re narrower in the knees than they are in the thighs and they’re narrower at the cuffs than they are in the knees. A good taper will flatter a man of any build because our legs naturally taper and clothing should show off the man who wears it. Those who are extremely skinny can get away with skinnier jeans and those who are bigger will want more space, but slim cuts are the only option.

They should feel pretty snug when you buy them because they’re going to break in and fit much better after some good use.

Make sure they’re not too long. A lot of this depends on how you like to wear your jeans. If you’re more blue-collar or rockabilly and like having them cuffed all the time, then buy them longer and get a proper roll so it doesn’t look like you’re wearing floods. If you don’t like them rolled, make sure they’re short enough that they don’t start to pool around your ankles. Of all the mistakes I’ve seen with clients in the past, the most common is buying jeans that are too long. They will visually shorten your legs and throw off your proportions.

Don’t wash them as often as you think. A good pair of jeans is kind of like a baseball glove or snowboarding boots – they’re made to adapt to and shape themselves around the man wearing them. If you wash your jeans after each wear they won’t ever be able to fit you as well as they could. If you spill anything that could stain or they start to smell, it’s a good time to throw them in the wash (although some die-hard denim heads will just put them in the freezer to kill the bacteria and keep wearing them after). If you bought your pants in the right size, they’ll be a bit uncomfortable after a wash because they’ll feel too tight. Wear them in for a few days and you’ll be good again.

casual dark jeans

Dress them down. Hiking, working on the car, football with the boys – I don’t really need to tell you to wear them in casual situations. Just throw them on and enjoy them.

high/low dark jeans

They’re perfect for a High/Low look. Pair them up with a tweed blazer, streamlined vest, button-up shirt, and dress shoes for a great balance between work and play. An outfit like this will make you the best-dressed man in any situation that doesn’t require a tie without looking like a dandy who can’t or won’t get dirty.

allen edmonds and jeans

Pro Tip: Wear them with dress shoes and thick, wool socks for a look that is dressed up but still very fall appropriate.

Avoid manufactured distressing, sequins, and carpenter pants. Everything about these jeans should be simple. They’re a background for the rest of your outfit and should be so simple that you could wear the same pair for two weeks straight without anyone noticing you haven’t changed them.

A lot of men like distressed jeans and I can certainly understand why. However, it’s important to know that your jeans should be distressed by you. I remember making fun of kids who would rub their skate decks on the curb to make it look like they were die-hards who would grind any ledge available, when really they couldn’t even ollie and just wanted to look the part. Same goes for pre-distressed jeans. If you don’t want your pants to look brand new, put in the time and work yourself. Wear them doing things that actually distress them. The great thing about natural distressing is that it fits what you do. I have a pair of Levi’s that have a perfectly worn mark in the right, rear pocket from where my wallet sits all the time. There’s no way to pre-distress that without it looking ridiculous.

I suggest by a couple pair because these will be a Staple in both regards – they wear with almost anything and you will wear them all the time. I’m happy with Levi’s that you can pick up for $30 but you can spend more on higher-quality, selvedge jeans from makers like A.P.C. or Naked and Famous as well.

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Meet The Author

Tanner is the founder and primary author of Masculine Style. He lives in Salt Lake City, Utah with his wife and two kids, and helps run Beckett & Robb - a men's clothing company built around custom suits and shirts.
  • rivsdiary

    another killer post.

  • tmp

    Everybody’s wearing those Allen Edmonds shoes. I was at a conference yesterday and three other guys had them on in addition to me.

    Finding jeans that fit is a major pain. I gave up and had the waist on my last pair tailored, which seems ridiculous. Jeans are all either way too loose and assume you’ve got a fat gut, or they assume you’re a scrawny fashion twink so if they fit the waist they are uncomfortably tight in the thighs and seat.

  • Travis

    Of course, you publish this the day AFTER I go jeans shopping. Oh well, I seem to have luckily gotten most of the important tips right anyway. One of the benefits of a former girlfriend who is still willing to help out as a personal shopper.

    • Tanner

      Haha. That is awful timing. Glad you were able to get the basics downs without the post though.

  • RioNomad

    I wear APC New Standards. I am not sure that they are slim enough below the knee though. I like a bit of a skinny fit, but not super skinny. Been contemplating having them tapered from the knee down.

  • Carl Sagan

    What brand and fit are you wearing the pics?

    Levi’s have been doing it right for so many years. Can’t go wrong with them.

  • Tanner

    Rio: I’m surprised the New Standards aren’t slim enough. From what I’ve seen they’re about as classic as a pair of dark jeans can be. That being said, if you want them slimmer, they’re definitely worth taking to a tailor.

    Carl: I’m wearing Levi’s 514’s for this shoot. I’ve been through three pairs of those jeans in the last six years and only one is now unwearable. The other two see a lot of rotation.

    • Stephen


      I’m looking on the Levi’s website and I don’t see any slim fit 514’s, only straight.

      • Tanner

        It’s all relative. You can go to the 513’s or even the 511’s if you want to get progressively skinnier.

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  • Revo Luzione


    Great post. Regarding fit, I’m one of those guys with a small waist, wider shoulders, and thick thighs. Jeans that fit me in the waist never fit my thighs, and usually squeeze my package more than is comfortable.

    So I’ve been getting jeans in a bigger waist size & getting them taken in. I have a great Russian taylor, who charges $12 a pair of pants to get the hem and the waist dialed in perfectly.

    At one time it was very common for people to re-blue their jeans with “bluing.” Something like this:

    Your thoughts on using bluing to darken up some jeans, por favor.

    • Tanner

      I’ll have to check that out Revo. I didn’t know it was something people still did anymore.

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  • OffTheCuff

    Out of everything I’ve tried, Old Navy Slim (not skinny) works well, is cheap, and appears to be a recent addition as of last year. Just don’t wash them and you’ll be fine. Good return policy if they wear in the wrong place, too.

  • Drake

    I’m another guy with bigger thighs, and I’m also 6’4″. I’ve had a nightmare time finding jeans that fit me. It was hard enough finding jeans with a 34 inseam before, but once I started lifting more weights and doing more squatting, my old staples of Levi’s 527’s just don’t fit anymore (not to mention they discontinued the line). I’ve found that Express Men’s “Blake” Style is so far pretty much the only thing I can get in and feel remotely comfortable now. I just hope they don’t discontinue those…

    • MasculineStyle

      Thanks for the heads up on this Drake. I have a lot of clients with similar frustrations and will be recommending these jeans to them in the future.